Composition of matter containing a



June. 18, 1940 Q COMPOSITION OF MATTER CONTAINING A CELLULOSE DERIVATIVEum M. Weber, West Englewood, N. 3., assignor to Ellis-Foster Company,Mcntclair, N. J.

No Drawing. Original No. 1,690,515, dated November 6, 1928, Serial No.62,293, October 13, s 1925. Application for reissue September 14,

1939, Serial No. 294,950

Clalms. (Cl. 260-16) This invention relates to a composition of mattercomprising artificial resins; and'relates 7 especially to resins ofcomplex constitution prepared from dryingand semi-drying oils and their5 fatty acids, an organic acid other than the fatty acids from oils, anda .polyhydric alcohol, such complex resins having incorporated with thema toughening agent, such as an ester or ether of cellulose, particularlynitrocellulose, and is a con- 0 unuauoh in part of my Reissue Patent No.

19,967 in which I have described the preparation of a complex resinfromresin and non-resin acids, and a polyhydric alcohol.

In the 'presentinvention resins prepared from drying or semi-dryingoils. such as linseed oil,

soya bean-oil or corn' oil, or their fatty acids, an

organic acid, such as phthalic' anhydride', and

glycerol, glycol, or other appropriate ."alcohol, toughened by means ofa cellulose esteror. ether, U are superior in that compositions soprepared'are less susceptible to outside influences, such as moisture,light, etc., particularly where such composition is to be used for thepreparation of lacquers or lacquer enamels, which would be .8 subject toexposure to the weather. Furthermore, when used for the preparation ofplastic compositions, films, molded articles of the shellac type, andthe like, their workability is somewhat superior to the resinspreviously produced.

a As stated in my Patent Reissue No, 19,967

the nitrocellulose esters are not compatible with a great manysubstances, but the resins pro-,

duced by means of the present invention as 'well as those mentioned inmy previous patent are a compatible in all proportions with thesecompounds producing products of great toughness.

As an example of a method of preparing the resinous compositions, thefollowingis cited:

Parts Glycerol; 94 Phthalic anhydride 160 China-wood oil 80 were heatedin a closed vessel fitted with a short air-cooled reflux condenser andhaving means for mechanically agitating the reacting constituents to atemperature of 235 C. Water was evolved throughout the reaction. Theproduct was a dark yellow hard brittle a resin containing a slightamount of free oil. The resin had a melting point of 73 0.. and an acidnumber of 56. It was soluble in a fifty fifty butyl acetate butylalcohol mixture and was compatible with nitrocellulose in allproportions. A iilm formed from butyl alcohol butyl acetate solu- Vselves in that they can be prepared with greater ease and with lessdanger of polymerization with consequent loss of the materials and ahomogeneous resin is produced containing no free oil 10 which wouldinterfere with the production of suitable articles for all purposes whenblended with a cellulose ester or ether.

As an example of a resin of this character I Parts Glycerol 94 Phthalicanhydride 1B0 Fatty acids (obtained from soya bean oil)--- 80 wereheated up to a temperature of 265 0., and go the product held at thispoint until a resin of suitable hardness was obtained.

The product'as obtained was a darkbrittle slightly tacky resin having amelting point of 71 (2., and an acid number of- 17. The resin wassoluble in butyl acetate and butyl alcohol mixture and was readilyblendable with nitrocellulose.

Films produced from a mixture of the resin and nitrocellulose wereclear, transparent, tough and were resistant to weathering conditions.

I Resins can also be produced from mixtures of fatty acids of'vegetableoils and vegetable oils with an organic acid and an alcohol which aresuitable for use for the purposes of the present invention. 36

For example, a resin was prepared from Glycerol ..L M Phthalic anhydride160 Fatty acids from castor oil -s 20 Corn'oil 60 by heating in thevessel described in Example 1 up to a temperature of 260 C." The resinso produced was light in color, somewhat turbid, hard and brittle withindications of containing a small amount of free oil.

When dissolved in a mixture of equal parts of butyl alcohol, butylacetate, and blended with a similar solution of nitrocellulose, it wasneces- 5e sary to add a small quantity of acetone in order to obtain aclear solution.

A film prepared from such solution was slightly turbid, tough andresistant to weathering conditions Blown oils such as blown castor oil,blown rapeseed oil and the like may also be used in Q g the preparationof a resinous complex, and resins prepared from this material aresuperior in that I they can be prepared at a lower temperature thanthose prepared from the fatty acids, or the vegetable oils, or mixturesof these, and produce a product which weathers extremely well. They havethe disadvantage. that they produce a coml. paratlvely dark coloredresin, and therefore are not as desirable for the preparation ofcompositions for use in 'clear lacquers or light colored plasticcompositions, but are confined to the preparation of pigmented lacquers,enamels, or

II dark colored plastic compositions where color is not of importance.

As an example Parts GlyceroL; 94

N Phthalic anhydride 160 Heavy blown rapeseed oil 80 ywere heated in theapparatus mentioned in Example 1 to a temperature of 235 C., and heldpreparation of the resinous complex, but it is to beunderstood thatother-organic acids such as benzolc. maleic, tartaric, succinic, and thelike, a

or mixtures of these, may also be used and be within the scope of thepresentlnvention. v

Vegetable oils and fatty acids obtained from vegetable oils other thanthose mentioned in the example can also be used, such as soya bean oil,linseed oil, cocoanut oil, China-wood oil, and the like, or productsobtained by blowing these oils;.

or mixtures of these.

What I claim is:

l. A liquid coating composition comprising a solution of nitrocelluloseincorporated with a resinous product resulting from the reaction ofphthalic anhydride and glycerol with fatty acid radicals of vegetableoil selected from the group consisting of the drying and semi-dryingoils.

2. A liquid coating composition comprising a solution of nitrocelluloseincorporated with a resinous product obtained from the reaction of fattyacid radicals of a drying oil with phtharic anhydride and glycerol.

3. A liquid coating composition comprising a action product of a fattyacid from a semi-drying oil, phthalic anhydride and glycerol.

HARRY M. WEBER. 1

solution of nitrocellulose incorporated with a

